Poly(α-hydroxy acid)s and poly(α-hydroxy acid-co-α-amino acid)s derived from amino acid

Basu, Arijit; Kunduru, Konda Reddy; Katzhendler, Jehoshua; Domb, Abraham J.

doi:10.1016/j.addr.2016.08.003

Cited by 45 publications

(24 citation statements)

References 129 publications

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“…The resulting fragments have greater solubility, are not toxic, and are metabolized and eliminated naturally by the organism. Examples of these polymers include polyesters from lactic acid and from glycolic acid (Basu et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Novel Eudragit® -based polymeric nanoparticles for sustained release of simvastatin

Rodrigues

Couto

Sinisterra

et al. 2020

Braz. J. Pharm. Sci.

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This paper reports on the development of nanoparticles aiming at the in vitro controlled release of simvastatin (SVT). The nanoparticles were prepared by the nanoprecipitation method with polymers Eudragit ® FS30D (EDGFS) or Eudragit ® NE30D (EDGNE). EDGFS+SVT nanoparticles showed mean size of 148.8 nm and entrapment efficiency of 76.4%, whereas EDGNE+SVT nanoparticles showed mean size of 105.0 nm and entrapment efficiency of 103.2%. Infrared absorption spectra demonstrated that SVT incorporated into the polymer matrix, especially EDGNE. Similarly, the differential scanning calorimeter (DSC) curve presented no endothermic peak of fusion, indicating that the system is amorphous and the drug is not in the crystalline state. The maintenance of SVT in the amorphous state may favors its solubilization in the target release sites. In the in vitro dissolution assay, the SVT incorporated into the EDGFS+SVT nanoparticles showed a rapid initial release, which may be related to the pH of the dissolution medium used. Regarding the EDGNE+SVT nanoparticles, the in vitro release occurred in a bimodal behavior, i.e., an initial "burst" followed by a sustained delivery, with the kinetics of drug release following Baker-Lonsdale's mathematical model. All these features suggest the nanoparticulate system's potential to modulate SVT delivery and enhance its bioavailability.

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Section: Introductionmentioning

confidence: 99%

Novel Eudragit® -based polymeric nanoparticles for sustained release of simvastatin

Rodrigues

Couto

Sinisterra

et al. 2020

Braz. J. Pharm. Sci.

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show abstract

“…To date, the intermolecular radical addition to ketones, , which is valuable to construct quaternary carbon centers, remains a formidable synthetic challenge. Lactates are important biological metabolites, which are precursors of poly-α-hydroxy acids for targeted drug delivery, and include many prescription drugs such as anticholinergic Oxybutynin and Glycopyrrolate (see Scheme b for structures) . The α-ketoacid is a readily available synthetic building block to prepare lactates by nucleophilic additions with alkyllithiums or Grignard reagents .…”

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confidence: 99%

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

Xie

Huang

et al. 2019

J. Am. Chem. Soc.

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The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-lightinduced intermolecular alkyl boronic acid addition to αketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C−C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.T he carbonyl group is a readily available building block for the synthesis of substituted alcohols. 1 While the nucleophilic addition to the carbonyl group is favorable and widely studied, the radical addition to the carbonyl group is difficult, as the resulting alkoxyl radical undergoes βfragmentation readily to reverse the reaction, especially for the radical addition to ketones (Scheme 1a). 2 To date, the intermolecular radical addition to ketones, 3,4 which is valuable to construct quaternary carbon centers, 5 remains a formidable synthetic challenge. Lactates are important biological metabolites, which are precursors of poly-α-hydroxy acids for targeted drug delivery, 6 and include many prescription drugs such as anticholinergic Oxybutynin and Glycopyrrolate (see Scheme 3b for structures). 7 The α-ketoacid is a readily available synthetic building block to prepare lactates by nucleophilic additions with alkyllithiums or Grignard reagents. 8 However, these reactions are susceptible to air and moisture, and the strong nucleophilicity of these reagents unavoidably result in undesirable side reactions. 9 To this end, the new synthetic approaches to lactates, especially from different mechanistic manifolds, are in high demand.Ketoacids currently undergo decarboxylative acyl radical formations in radical reactions, and their engagement as the radical acceptors remains unknown (Scheme 1b). 10 Organoborons are environmentally friendly and readily available, and are stable synthetic building blocks with Lewis acidity. 11 In this communication, we report the first alkyl boronic acids radical addition to ketoacids with the Lewis acid activation from organoborons, which can be extended to alkyl dihydropyridine radical addition to ketoacids in the presence of external boron reagents (Scheme 1c).

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“…On the other hand, polyesteramides, like polyamides, should have better thermomechanical properties due to the formation of hydrogen bonds between amide groups [ 176 ]. Thus, the combination of amide and ester bonds in one polymer presents additional opportunities for the creation of new materials with desirable properties for biomedical application [ 177 , 178 , 179 , 180 , 181 ]. Various derivatives of hydroxy and amino acids, dicarboxylic acids, cyclic depsipeptides, diols, diamines, amino alcohols, lactams and lactones can be used for the synthesis of polyesteramides [ 182 , 183 , 184 , 185 ].…”

Section: Enzymes and Polymers Produced With Themmentioning

confidence: 99%

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Nikulin

Švedas

2021

Molecules

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Trends in the dynamically developing application of biocatalysis for the synthesis and modification of polymers over the past 5 years are considered, with an emphasis on the production of biodegradable, biocompatible and functional polymeric materials oriented to medical applications. The possibilities of using enzymes not only as catalysts for polymerization but also for the preparation of monomers for polymerization or oligomers for block copolymerization are considered. Special attention is paid to the prospects and existing limitations of biocatalytic production of new synthetic biopolymers based on natural compounds and monomers from biomass, which can lead to a huge variety of functional biomaterials. The existing experience and perspectives for the integration of bio- and chemocatalysis in this area are discussed.

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Poly(α-hydroxy acid)s and poly(α-hydroxy acid-co-α-amino acid)s derived from amino acid

Cited by 45 publications

References 129 publications

Novel Eudragit® -based polymeric nanoparticles for sustained release of simvastatin

Novel Eudragit® -based polymeric nanoparticles for sustained release of simvastatin

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

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